Potassium Carbonate → HCID 69192521, compound

HRID 1187399Notes

Reaction equation

HRID 1187399 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][N:14]1[C:26]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:16]=[CH:15]1)(=O)C>CO>[N:14]1([CH2:13][CH2:12][CH2:11][OH:10])[C:26]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:16]=[CH:15]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69192155HCID 69192155, compound

Product 1

HCID 69192521HCID 69192521, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid potassium carbonate (2.68 g, 19.4 mmol) was added to a solution of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl acetate (3.50 g, 12.9 mmol) in methanol (65 mL) at room temperature. The mixture was stirred for 3 hours, then the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane (150 mL) and water (75 mL). The organic layer was washed with brine (75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a brown semi-solid that was triturated with dichloromethane and isolated by filtration to afford 0.48 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-50% CMA in chloroform) to provide an additional 0.67 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between dichloromethane (150 mL) and water (75 mL)
  3. washThe organic layer was washed with brine (75 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a brown semi-solid that
  8. customwas triturated with dichloromethane
  9. customisolated by filtration

Sources & evidence

ORD record
ord-e883643177bb4dc8a7c3a9da9ceb8724
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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